


Cherry Popping

by TatsusFineAss



Category: Naruto
Genre: Alternate Universe - College/University, Alternate Universe - Modern Setting, Bisexual Male Character, Blow Jobs, First Time Bottoming, Gay Sex, Kissing, Loss of Virginity, M/M, first time gay sex
Language: English
Status: Completed
Published: 2020-02-24
Updated: 2020-02-24
Packaged: 2021-02-28 02:47:26
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 6,188
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/22886545
Author URL: https://archiveofourown.org/users/TatsusFineAss/pseuds/TatsusFineAss
Summary: Itachi, a university student, decides to go on a gay dating app to see if he is bisexual or not. He instantly clicks with Shisui, another student on the other end of the country. During summer, they decide to meet up, for Itachi to experience his first time with a man.
Relationships: Uchiha Itachi/Uchiha Shisui
Comments: 6
Kudos: 91





	Cherry Popping

Shisui’s phone pinged from on his desk. Sitting up from the top of his bed, he stretched out a hand and checked his notifications. 

“Okay, I think I’m here.” 

Smiling, he opened up the message, his thumbs quickly tapping away to reply.

“Can you see the vending machine outside? There should be a green car next to it too.”

The three little dots popped up, indicating the guy who was coming up to his apartment was texting back. 

“Yes, I see them both. You’re number 13, right?” 

Quickly changing his keyboard, Shisui sent a quick thumbs up and love heart emoji. He wasn’t really one for using those things, but the boy he had been texting had a habit of using them when he was feeling excited, nervous, curious, and so he thought it would be cute to do the same. At that moment in time, he felt incredibly excited. 

Itachi, the guy he had been texting quite a lot for the past month, was finally coming up to his apartment. They had met on a dating app, and from the moment Shisui laid eyes on the other, he felt a great, sudden urge to meet with him. Itachi’s profile looked like it had been made with a great deal of care. The only two pictures he had uploaded were both of himself in bed - one with his hair wet, probably just out of the shower, spread out on the pillow as he looked up at the camera, a kind of - innocent expression on his face. The other was with his hair tied back into a loose bun at the top of his head, an oversized t-shirt hanging off his shoulders and showing off his collarbones, his glasses slipping down the bridge of his nose. In both pictures, Shisui felt a rare sense of purity and beauty that he hadn’t ever seen since he had made an account on the app. 

But it wasn’t just Itachi’s pictures that made him desperate to see him. His bio, as well as their conversations, made Shisui itch to lay his hands on the other. It appeared that Itachi had grown up in the same city as he had, but had moved away to the other end of the country when he went to university. He was the same age, 24, and he was questioning whether he was bisexual or not. His profile hinted he wasn’t looking for anything serious - just someone who could confirm whether or not he was imagining this new urge to be held by another man. Shisui was in fact, looking for something serious, after a solid year of hook up and hook up after a one night stand. But, if Itachi wanted to simply be taken by a man once, then Shisui was more than willing to perform that request. 

Their conversations lasted hours. They went into great detail talking about their sexual experiences, their likes, dislikes, things Itachi should do to prepare. They were simply waiting on the day that Itachi was coming back to his hometown for summer vacation, and when he announced he was travelling back mid June, Shisui could hardly contain his excitement. 

Standing up and stretching, he gave a final glance around his room. The bed was made, his desk was tidy, he was fully stocked up on the things the two of them would be needing. Everything was in check. He was also fully aware that Itachi would be nervous. He seemed ever so slightly shy over their texts and phone calls, so there was no use in pouncing on him from the get go. The two just needed some time to relax together before anything could go down.

A timid knock came from the other side of his door. His student apartment was tiny, so he only needed to talk a few steps from his bed to unlock it. 

“Hey,” Shisui’s voice ever so slightly hinted at a smidgen of nervousness. He had had multiple one night stands and so on, but somehow this sort of thing felt different. He and Itachi had been talking for well over the amount of time most of his other hooks up had talked. They had called, and somehow, Shisui felt an incredible sense of responsibility. If he messed up the mood or the feeling, Itachi might be freaked out to ever try something like that ever again. A lot was riding on his abilities. 

“Hey,” Itachi replied. He was standing in the doorway, his bag slumped over his shoulder, his hair tied up in a messy ponytail at the back, strands of his hair gently resting against his collar. A light, airy brush of pinkness flushed across his cheeks, hinting that he was a little shy. 

Opening up the door wider, Shisui gestured for Itachi to come in, holding out a hand to take his bag. 

“Come on in, I’m sure you’re tired after the long train ride up here,” he said as Itachi wandered into his apartment, handing him his bag, and took a glance around the room. He seemed a little out of his comfort zone - like he had never appeared at a guys house before for sex. But, then again, Shisui knew that was the case - they had already discussed that over their messages. As Itachi slipped off his shoes at the doorway, Shisui placed his bag down at the desk and gestured towards the bed.

“Go ahead and sit anywhere you like - the bed is fine. Do you want something to drink?” he said, wandering over to the small fridge in the kitchen space in front of his bed. Opening it up and crouching down, he peered inside. 

“There’s tea...iced coffee...beer...and that’s about it,” he said, reaching out for a beer for himself. 

Itachi sat himself down on the bed. It was a lot softer than his student apartment bed. Although he was trying his best to not appear so, he was rather tense. This was his first time, after all, going to someones house for a one night stand, and his first time with a man as well. The last thing he wanted to do was to show that he was on edge - he didn’t want to seem lame or inexperienced, but it seemed the more he tried to compose himself, the worse his jitters got. In person, Shisui looked a lot more handsome than his pictures. Of course, his pictures did not look bad at all - but he was much taller than he expected, and his face had a gentle softness to it that made him feel at ease and flustered at the same time.

‘Maybe alcohol will calm me a little,’ he thought.

“I’ll have be-” he was cut off by Shisui tossing a beer can up into the air and passing it over to him. 

“You took your time deciding so I decided for you,” he said, sitting himself down on the bed, resting his back against the wall. Opening his can and taking a sip, his eyes wandered up and down the man sitting on the bed beside him. The first thing that caught his attention was the tantalisingly long, jet black hair that was half up, and half dropping onto his shoulders. Shisui had a thing for guys with long hair, and he couldn’t help but extend his arm and tangle a few strands of it between his fingers.

‘I can’t wait to mess it up even more…’ he thought.

“Oi, you look so nervous Itachi. Don’t worry, I’m not going to pounce on you. You can relax,” he said, his voice sounding ever so slightly turned on as his fingers gently rubbed at the soft delicate hair between them.

Itachi let out a sigh, allowing his shoulders to drop down, shifting his back up against the wall as he downed half of his beer. 

“I - yeah. I do feel a little nervous. But it isn’t because I think you’re going to pounce on me - I’m just…” Itachi’s voice was a little crackly after drinking so much beer in one go, and he searched for the right words to say.

Letting go of Itachi’s hair, the back of his finger lightly brushed against his cheek.

‘His cheek is pretty warm...he must be feeling shy,’ he thought to himself.

“Are you feeling a little scared?” 

Itachi nodded, shifting his head to rest on its side against the wall, his eyes focused on the man in front of him. 

“Yeah...It’s my first time with a guy, so I’m really not sure what to expect…” 

Watching as Itachi’s face began to bruise a delicate shade of pink, and hearing the smoothness of his voice, even Shisui couldn’t stop his own blush from forming on his face. 

‘He’s way too innocent...he has no idea how attractive he looks right now.’ 

Wanting to stretch out a hand and push Itachi’s face into a kiss, but knowing that it was far too soon to start anything like that, he distracted himself with another drink of beer. 

“I sound like a broken record, but don’t worry, seriously. I know what I’m doing, and I’ll make sure you don’t feel uncomfortable or pain at all. And you can always tell me what’s good and what’s not good, right?” He could feel his face redden up. Although Shisui had had sex with plenty of guys, he had never done anything with a complete newbe, and there was something really enticing about the thought of taking that innocence away from the guy sitting next to him, and melt him into his shape. 

Taking another sip of beer, Itachi smiled, brushing a few strands of hair back behind his ear.

“You’re...really experienced with men, aren’t you?” His gaze moved from the handsome man in front of him, down to his beer can, where he began to fiddle with the pull tag. 

Gulping down the rest of his beer, Shisui got up to get another from his fridge. 

‘What the fuck? Why am I feeling so bashful? He’s not doing anything sexy right now - he’s just chilling on my bed!’ 

“W-well! Saying it like that makes me sound like a slut,” he laughed, scratching the back of his neck as he sat back down, opening the can up and taking a drink. He wanted to down the whole thing, but that wouldn’t be any good. If he got drunk, he might be more rough - and he didn’t want Itachi’s first time to be scary. 

“But, I guess I have experience. So I just...don’t want you to worry about anything. We can take it slowly, and I’ll do anything you want to make it good.” 

‘What the fuck am I saying…’ 

“Then, I’ll be in your care for tonight. Please be gentle with me,” Itachi’s voice was a little lower, and the way he spoke hinted at a careful planning of words - he didn’t want to come across as weak, but he didn’t want to push himself into something that he couldn’t handle. 

Several beers and a good few hours later, the two of them had much higher spirits. Itachi was no longer nervous, as Shisui had done his best to take his mind off of anything troublesome, and Shisui was able to somehow control the urge to take charge of the other. Despite having had a good few drinks, he didn’t feel that drunk, but it was clear from the way they talked and laughed that they were both feeling rather tipsy. 

“Oi, oi, Itachi,” Shisui said, his legs perched up against his chest as he opened his last can of beer, watching the other man walk back to the bed after heading to the bathroom. “Why did you decide to go on a gay dating app? And why did you swipe right on me?” The conversation the two had been having up until then was focused a lot on school, stories, complaints about their family, and so on. But he could feel a slight change in the air as Itachi left the bathroom. There was no more alcohol, only one can left, and throughout their talking and laughter, Itachi had clearly eased up a little. He had been holding onto Shisui’s finger as they talked, leaning against his shoulder as he drank, and staring down at the occasional glimpse of his chest showing from his low cut t-shirt. Shisui could tell that this was the perfect time to bring up the raunchier kind of topics, which could let him slip into kissing the other easily. 

“Hm. That’s a good question.” Itachi sat himself down on the bed once more. “Well...I just always knew I was attracted to men and women...but I’d only had girlfriends up until now. So when I went to university, I was kind of hoping to experiment more with men but...I found myself in a totally unknown world. So I just downloaded an app to try and find men I was attracted to...and you were the first guy I liked.”

Hearing that he was the first Itachi liked, Shisui began to feel ever so slightly bashful again. To snap him out of it, he took another sip of his beer. 

“Oh...I was the first one?” 

Taking the beer from Shisui’s hands, Itachi took a sip himself. 

“Yeah, you were. I knew I wanted to be with a guy who was taller than me, and I thought you looked really manly in your pictures. When it said you were gay, I thought you must have had a lot of experience with men, and that, letting you be my first, might feel good for me too. So when you liked me back, I was surprised. Since we hit it off right away, I didn’t use the app anymore.”

Sitting up and away from the wall, Shisui’s eyes widened in surprise. 

“I...wait...you mean to tell me, you swiped right on me, we matched, and you never used the app again?” 

Itachi reached over at the desk where his phone was, unlocked it, and handed it over to Shisui.

“I deleted it after you gave me your Instagram. It’s gone from my phone now. You can check it if you like.”

Shisui looked down at the apps Itachi had. There were the usual - social media, mail, a photography app, a calendar app, and some sort of recipe app. That was it. Clicking the phone to lock it again, Shisui rubbed at his eyes and shook his head, in an attempt to process the information better.

“But...don’t you want to use the app again? You could find yourself a boyfriend or a girlfriend when you go back to university.” 

Placing his phone back on the desk, Itachi took another gulp of beer before handing the can back to the other. 

“I don’t want to date anyone though. Once I go back in September I’ll be too busy. I just...really wanted to try having sex with a man before I graduated, so I knew if I was bisexual or not.”

Nodding along, Shisui made a face that let Itachi know he understood.

“That checks out. But you were pretty adamant about being the one who bottoms, right?” 

Remembering their previous conversations, Itachi covered his face with his hands and let out a groan. 

“I...yes...do we need to...talk about that…?” 

Shisui grinned, and in his tipsy mood, brought his hand upwards to give another feel of Itachi’s long hair. 

“I’m just curious why you wanted that to be that way. It’s good for me, since I only ever top. But guys who just want to experiment usually don’t want to be the one stretched out.” 

With Shisui now playing with his hair again, and the conversation turning more sexual, Itachi’s heart began to pound. He could tell the energy...the atmosphere in the room, it was hinting that something was about to go down. Something was going to begin. Something was going to be taken from him. 

“Well...I wanted to be the bottom because it felt good. When I did it...myself.”

At this, Shisui’s mouth opened and let out a small sound of both shock and arousal. Of course, Shisui knew some of the men he slept with obviously masturbated using their ass before. It was a given. But he didn’t think Itachi seemed like the type to do such things - let alone tell anyone about that kind of activity. 

“You...you use your fingers when you jerk off?” He felt crude for asking such a question out loud, but the curiosity that was bubbling away inside his brain was messing with his senses. 

“Well, I...no, not now...I have to-” Itachi looked up from out of his hands, his cheeks now completely red with shyness. He noticed how closely Shisui was, and to stop himself from getting too overly embarrassed, he pressed two fingers on the other mans forehead, pushing his face slightly further away.

“O-Oi! Shisui...you’re too close.”

“You were going to say toys, right?” 

With his face now completely red in shame, Itachi felt the insides of his thighs shake. He shouldn’t have mentioned something so gross as that, he thought to himself. 

Reaching up both of his hands, Shisui’s fingers searched for the hair tie that was now barely holding all of Itachi’s gorgeous hair up. Gently pulling at it, he let all of the smooth black hair fall down to almost his backside, all the way down his back. That was the longest hair Shisui had ever seen on a guy - and it turned him on to no end. He had a thing for long hair, especially long black hair, and Itachi had the best he had seen. 

“Oi...Itachi...don’t be so embarrassed,” he said, one hand being placed on the other mans cheek, while the other ran through the luscious locks, brushing some against his ear and rubbing at the ends. 

The look in Itachi’s eyes gave Shisui a clear indication that he was expecting something from then on.

“You’re really good looking, you know that?” Shisui’s voice had suddenly turned a little more serious. “Your hair is stunning, and you have a really cute face.”

Itachi lifted up his hands and placed them on Shisui’s, which were now ever so softly holding his face, the two thumbs rubbing tiny circles on his cheeks.

“I’m...I’m really nervous Shisui...I’ve never been with a guy before,” Itachi’s voice was cracking, and there was a much heavier atmosphere in the air, a stiff thickness that made both men on high alert. Now was the time Shisui could take the opportunity to make his move. The touch of his hand upon the other tightened into a more anxious grip.

“I know, that’s why I’m going to be extra gentle with you, you know that, right?” Leaning in, Shisui planted a delicate kiss on the other’s forehead.

‘I shouldn’t just straight up kiss him on the lips...he’s feeling really sensitive and I need to ask before I do anything too serious.’ 

Avoiding eye contact, Itachi shifted his gaze downwards, his toes curling in anticipation, his hands holding onto the larger ones that held his face ever so tenderly. 

“I know you’ll be gentle...but I also want you to feel good and...I’m just nervous I’ll suck at it...you won’t be mad at me if I’m no good?” 

Everything Itachi was saying was beginning to send a shot of longing in Shisui’s chest. His delicate, soft way of speaking, and his insecurity, his inexperience, along with the knowledge that Shisui himself was going to be the one to bring this man into a brand new world of pleasure, was something that he just couldn’t contain.

Moving his thumb to just under Itachi’s lip, which had already began to tremble, Shisui gave it an affectionate nudge. 

“Can I kiss you?” He could hear his own voice had lowered, the crackling in his throat indicating a growing desire to pin the other down and ravish him. 

“Yea-” Itachi had little time to finish his answer, as Shisui took no time at all pushing him backwards onto the bed, one hand holding onto one of Itachi’s wrists, the other hand going straight for the long black hair that was now spread out onto the pillow, his fingers gripping onto some as his hand pressed against the other mans head.

Their lips connected, Shisui’s tongue confidently entering Itachi’s mouth, feeling all around the inside of his mouth, rubbing against his tongue, the movement causing a trickle of saliva to run out of the corner.

For Itachi, this first time kissing a man wasn’t far different from the girls he had kissed - but he could tell that Shisui was clearly displaying a level of dominance in their kiss that he had not felt with a woman before. As Shisui’s tongue filled up Itachi’s mouth, his hand moved from the other mans wrist to just above his belt, tucking his hand under the loose summer t-shirt, pulling it up as his hand reached upwards to finally rest on Itachi’s chest.

At the feeling of his nipple being brushed up against, Itachi let out a slight sound of surprise, which broke their kiss. Taking the opportunity, Shisui took a good look at the boy below him. The redness of his cheeks, the tremour in his lips, the hint of fuzziness glazing over his eyes all indicated to Shisui that he was feeling something good.

‘I need to calm down...I can’t just take him immediately...there’s so much to prepare…’ 

“Do you like your nipples being touched?” Shisui ventured an ask, licking his lips at the sight of Itachi pushing out his chest and taking a look at the hand that was beginning to lightly pull and tug at his left nipple.

“I...never tried it…” 

Sitting upwards, Shisui ran a hand through his hair before pulling off his shirt, throwing it across the room, which gained what looked to be a twitch from inside Itachi’s pants. 

Looking at the half naked man that was now straddling him, Itachi’s heart began to beat in what could have been a mixture of fear, excitement, and anticipation.The way that Shisui moved showed that he had built up so much confidence and experience, and a gentle dominance protruded from him. 

“Well then, let’s try it out,” Shisui smiled, leaning his head down to plant a few soft and small kisses on the nipples below. They were a little larger than most of the men he had slept with, pinker and smoother as well - but even at the faintest hints of stimulation, they began to grow hard. Once they were were hard enough to suck on, Shisui opened up his mouth, his tongue readily flicking over the cute pinkness, his mouth encapsulating around, and one of his free hands kneading and pulling at the other. By the feeble muffled moans coming from the man below him, matched with the consistent twitches that came from from Itachi’s erection pressing up against his stomach, Shisui knew he was doing something right.

‘Take your time...make it feel good for him...take it slow…’ he had to reassure himself in his brain. All of his instincts were telling him to rough it up and make a mess of him - but he couldn’t do that. Not for his first time.

“Does that feel good? Your nipples seem really sensitive,” Shisui said, resting his chin on itachi’s chest, his fingers continuing to flick and press up against the now wet and slightly puffy nipples beside him.

Removing the arm that was laying over his mouth to ensure he didn’t get too loud, Itachi shyly looked down.

“Yeah it’s good...I’ve never touched them before like that…” 

Shisui could feel the fast drumming of Itachi’s heart, matched with the raising of his chest with each breath and the foggy glaze in his eyes, let him know that the man he was resting on was really starting to feel good. Staring up at him, Shisui felt his own heartbeat begin to speed up. The guy he was going to take tonight was far more beautiful than anyone he had ever dated. Those long, thick eyelashes, the darkness of his eyes, the waist length hair that was so soft to the touch. He wanted to blow this man’s mind wide open with pleasure. 

He couldn’t help but reach out his fingers to once again lock in some hair in his grasp, his mouth opening up to kiss and suck on the milky white neck beside that dazzling black hair he couldn’t get enough of.

“You’re really…gorgeous,” he groaned into Itachi’s ear, his own hips now hungrily grinding against the other mans crotch. “Can I...finger you?” 

For the next half an hour, Shisui took great care in stretching Itachi out. As the other man lay there, his arms behind his knees, keeping his legs spread open, Shisui expertly inserted his fingers, aided with a generous helping of lube, which allowed him to squeeze inside the tightest hole he had ever touched. His fingers rubbed along the insides which were clamping down on him, while his mouth opened up and sucked on his partners reddened hard on right to the back of his throat, coating Itachi’s cock in strands of frothy saliva. Spreading out the three fingers he had managed to get inside, he began to open up the hole as best he could, making sure his middle finger reached up to that special spot inside. 

Feeling the sensation of being stretched, his prostate massaged as his cock was being eaten up, Itachi could do nothing but lay there, his eyes ever so slightly rolling up in his head, his legs quivering as he struggled to contain his moans. 

Sitting upwards, Shisui spread more lubricant on his fingers and on Itachi’s dick, before he began to gently pump his fingers in and back out, his other hand squeezing around to squelch and tug in a steady but rough hand job. With each stroke and each insertion, Itachi’s mouth opened up to let out a groan.

“Is that good? I can feel you tense when I reach up here,” Shisui said, pressing his middle finger against Itachi’s prostate as his eyes took in every inch of the gorgeously soft and weakened body on his bed.

“I feel...my stomach is hot…” Itachi couldn’t bare to look at the man whose fingers were giving him so much pleasure. This was far better than what he had imagined - Shisui was not only patient and tender with him, but it was clear from the bulging thickness pressed up against his own boxers that getting Itachi off was also getting him off. 

“That’s a sign you’re about to cum,” he said, tightening his grip around the hardened erection between his fingers, the erotic sound of lube melting together filling the room.

Moving his arms from over his eyes, Itachi’s fingers stretched outwards, lightly pressing up against Shisui’s stomach. It was strange feeling body hair on that part - he wasn’t used to it. 

“W-wait,” he said, his breath becoming heavier. “I don’t..want to cum just yet…” Laying deep under his feelings of ecstasy was a growing sickly feeling of guilt. He didn’t want to be the only one feeling good, and he certainly didn’t want Shisui thinking he was just a lazy good for nothing who only lay there.

His eyes hovered over the small tent that had been there for a while, the stiffness which was propping up Shisui’s boxers.

“Can you...teach me how to do it?” 

Raising an eyebrow, Shisui cocked his head to the side. 

“Teach you how to do what?”

“Suck…” Itachi’s foggy, lust filled eyes didn’t break contact with the growing fondness found within Shisui’s. His fingertips slipped from his stomach, to ever so slightly cup at the warm hardness protruding.

“You want me to teach you how to give a blow job, right?” Shisui smiled, removing the sticky fingers from inside, and stopping his movements around Itachi’s cock. 

‘He’s never done it before, so he’ll need a lot of guidance,’ he thought as he wiped his hands with a towel. ‘But that innocent face he just made…’

Sitting himself down with his back against the wall, he instructed Itachi to perch in front of him. The look of curiosity painted on Itachi’s face was enough to make him want to ram everything in. His erection was pushing against the fabric of his boxers, and as he slipped them off in front of Itachi, it slapped against his stomach. 

“You’re much bigger than me...I’m a little jealous,” Itachi said, his fingers edging over and gripping the base. 

Placing a hand on Itachi’s cheek, Shisui smiled.

“Don’t compliment me too much, it’ll just go to my head. Am I bigger than your toys?” 

Itachi nodded. His eyes ran up and down Shisui’s length, a mixture of lust and confusion on his face.

“You’ve never done this before, right? I’ll teach you,” Shisui said, his thumb stretching over and teasing Itachi’s bottom lip open. 

“First, take out your tongue. 

Yes, like that. Now start to lick at the base.

Good, right there. Run your tongue up the back, make sure your tongue is still wet.

Mn. Just like that. Once you get to the tip, roll your tongue around, like I did with yours.”

With each command Shisui gave, Itachi submitted, doing everything as best he could.

“Good, now, open your mouth up nice and wide, and take it inside your mouth. Keep your tongue straight, and suck the way you’d suck on some candy.” 

Itachi did just that. His mouth opened up, clumsily and readily taking in most of Shisui’s inches, his throat making some gurgling and heaving sounds as he got used to the thickness inside. Each time he glided his lips across, he looked upwards, his eyes looking for some sign that he was doing well. 

Shisui could tell that this was his first time ever giving oral sex on a man. His own hand helped guide Itachi’s head, giving it some reassuring rubs on the cheek. 

‘His rhythm is all over the place and he can’t get it all the way back just yet,’ he thought, but the feeling of the warm curiosity of Itachi’s tongue wriggle around, his eyes closed and his head fell back against the wall.

“Good?” Itachi asked as he removed Shisui’s cock from his mouth, taking a few deep breaths before sucking it back inside.

“Mn. You’re really good at this for your first time. Can you take me a little further back?” 

Putting both hands on the back of Itachi’s head, Shisui’s fingers rubbed at the hair between them, his palm softly pushing the other’s head down. With the faint sound of gagging being suppressed , Shisui closed his eyes and lay his head back, feeling the inexperienced warmth grip around his length as he pushed Itachi’s face to press against his pubic hair, his cock completely inside.

“Just like that…”

Feeling the thickness at the back of his throat, Itachi began to choke, strings of saliva frothing out his mouth as he pulled back to breath. 

“You’re too - big to fit it all in,”Itachi mumbled as he caught his breath. 

Shisui lightly stroked the others cheek.

“Shall we try and fit me inside somewhere a little smaller now?” 

Shisui wanted to Itachi to keep on sucking him. The innocent and inexperienced little pops and lip smacks were driving him wild, but the thought of entering into a completely new and unexplored area was making him shiver. He was going to take it gently, but he needed to begin soon before he exploded.

Laying on his back, Itachi’s face lit up with a mixture of excitement and an unexpected dread. With his legs spread open and his hands behind his knees, his lower back began to shake. 

“I-is it going to hurt?” 

Spreading lube on both his cock and surrounding the other’s hole, Shisui smiled, shook his head, and drew himself closer, aiming the tip just outside of the entrance.

“You’ll feel something hot stretching you out, but I’m going to go as slow as I can. You can tell me if it’s too much,” he said, one hand holding himself in place while the other reached out to cup Itachi’s face. 

As he pushed inside, the feeling of the hot and pulsating tightness wrapped around him, sucking him up. He slipped in, centimetre by centimetre, sweat dripping from his forehead as he closed his eyes, rejecting the instinct to just push right to the back.

Itachi lay, his legs shaking, head thrown back, moaning every so often as each of Shisui’s inches stretched his insides. He was sweating, swearing under his breath, panting, and trying so hard not to cry out.

It took another twenty minutes before Shisui could finally begin to thrust the way he wanted. Itachi needed time to breath and get used to the sensation, but once he was ready, there was no longer any feeling of pain. The pure bliss of being completely filled, matched with the strong grip Shisui had on his arms, the deep grunts from his throat, and the sound of the bed creaking beneath them. 

For Shisui, he had never felt such a tight grip before. He hadn’t ever slept with someone who’s first man was himself, and so the soft and mushy pressure around his length was driving him crazy. He was able to keep just enough of his sanity to ensure he thrust up into that special place deep within, that would make the other’s legs wrap around his waist. Itachi’s face was covered with both of his arms, his chest rising quickly as he panted, but it was a sight worth all of his effort. 

“Oi, Itachi -” The sweet constriction of Itachi’s newly lost virginity squeezed tighter, causing Shisui to come to the horrific realisation that he was about to come. “Itachi...look at me…” 

Reaching out a hand to tug at the black locks beneath him, Shisui’s thumb gently nudged at the arms covering Itachi’s face. 

“I’m...at my limit,” Itachi said, his fingers gripping his tight erection, his wrist moving to jack himself off. The feeling of the silky hair in his touch, the sight of Itachi, eyes glazed over as he focused on the gorgeous feeling of pleasure as his pink tiny hole was being stretched out, Shisui felt his own climax approaching. 

With just a little more focus, Shisui’s thrusts became more direct, aiming right at the back of Itachi, filling him up as best he could, he could feel himself edging closer and closer.

“Fuck you’re so tight, how does it feel?” His eyes were squinting, as he tried hard not to come without warning.

In between deep breaths, Itachi’s mouth opened up, a little saliva dribbling from the corner of his mouth. “So - much better - than my toys…”

“I bet, is my cock good?” 

“Y-yeah, I feel like...my stomach is melting…” 

Rubbing the sweat from his forehead, Shisui bent down, spreading his knees and slamming as hard as he could, his tongue wiggling its way into Itachi’s mouth. 

Before long, Itachi’s toes were curled up, his ass clenching down as he cried out, the climax of his first time spraying up onto his tummy, filling up his belly button, dirtying the sheets. Shisui then allowed himself to release, the excitement and anticipation of being this mans first time bursting out of him, squirting up inside the freshly stretched hole. 

_________________________________________________________________________

Although both of them fell asleep at exactly the same time after they had had their shower, Shisui woke up a lot later than Itachi had. At 10am, his alarm went off, and he instinctively clicked it on to snooze. 

Sitting himself up, the bed felt surprisingly light. The numb feeling he had gotten from the intensity of the night before still lingered on his skin, his fingers wanting to reach out and touch Itachi some more. 

But he was gone.

‘Where’s is he?’ 

Strolling around his tiny apartment in the nude, he felt the strong brush of sunshine come through his windows and paint itself onto his skin. 

There was a note on his desk, on top of his text books.

“Hi, I got up early and left. I’ve never done this before, so I didn’t know if I should keep sleeping until the morning when you woke up. Last night was amazing, and it confirmed so much in my mind. If possible, I want to meet you again. Can you wait until I finish my next semester at university? I’ll be home for two months, and we can see each other again.”

Flicking on the kettle to make himself some coffee and switching his phone on, Shisui ignored the several texts and notifications, and scrolled through to his texts to Itachi. 

“I’ll wait for you.”

**Author's Note:**

> Yo! This fic took forever to write up. I wrote so much and in the end it didn't turn out the way I wanted it to. But, it had been in my folder for like a month and a half so I figured I ought to just finish it and pump it out. I hope it's okay! I hope you guys can enjoy it, and if you do, please leave me a little comment :) it gives me lots of "ser of tone in" :) 
> 
> Also, if you have any requests of Naruto fanfics, lemme know!


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